Thiourea‐Promoted Cascade Dihalogenation‐Cyclization of Cyclohexadienone‐Containing 1,6‐Enynes-Reference-Cited by-同舟云学术

Thiourea‐Promoted Cascade Dihalogenation‐Cyclization of Cyclohexadienone‐Containing 1,6‐Enynes

Published:2023-01-31 Issue:4 Volume:365 Page:482-489
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Zhao Jia‐Ying¹,Liao Qi¹²,Zhang Jian‐Wei¹,Lin Guo‐Qiang¹,Wang Zhengtao²,Gao Dingding¹^ORCID,Li Qing‐Hua¹^ORCID,Tian Ping¹^ORCID

Affiliation:

1. The Research Center of Chiral Drugs, Shanghai Frontiers Science Center for TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine Shanghai University of Traditional Chinese Medicine 1200 Cailun Road Shanghai 201203, People's Republic of China

2. The MOE Key Laboratory for Standardization of Chinese Medicines, Shanghai Key Laboratory of Compound Chinese Medicines, Institute of Chinese Materia Medica Shanghai University of Traditional Chinese Medicine Shanghai, People's Republic of China

Abstract

AbstractOrganohalogens play an important role in the drug discovery and functional materials. However, the convenient preparation of organohalogens still remains a challenging task. Herein, we report a metal‐free cascade dihalogenation‐cyclization of cyclohexadienone‐containing 1,6‐enynes in a biodegradable solvent to generate the dibrominated cis‐tetrahydrobenzofuran‐5(4H)‐ones and cis‐dihydrobenzopyran‐6(5H)‐ones respectively bearing 1,4‐dibromobut‐1‐enyl subunit in trans‐trans and trans‐cis form. A subgram‐scale experiment and several downstream transformations are presented for elaborating the synthetic utility. Moreover, the potent anticancer activity is observed against MDA‐MB‐468 cells for the corresponding products.

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Funder

National Natural Science Foundation of China

Science and Technology Commission of Shanghai Municipality

Shanghai Municipal Education Commission

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202201185

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